1. Field of the Invention
This invention relates to a process for producing triazoline derivatives. More particularly, the present invention relates to a process for producing N-(2-fluorine-substituted-phenyl)thiazoline derivatives represented by the general formula (I) ##STR2## [wherein R is a haloalkyl group of 1 to 5 carbon atoms and R.sup.1 is a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, an alkyl group of 1 to 6 carbon atoms having halogen atom substituents, a cycloalkyl group of 3 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms having halogen atom substituents, a cyanoalkyl group of 2 to 4 carbon atoms, an alkenyl group of 2 to 6 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a lower alkoxyalkyl group of 2 to 6 carbon atoms, a lower alkylthioalkyl group of 2 to 8 carbon atoms, a lower alkylsulfinylalkyl group of 2 to 6 carbon atoms, a lower alkylsulfonylalkyl group of 2 to 6 carbon atoms, a lower alkoxyalkoxyalkyl group of 3 to 8 carbon atoms, a hydroxycarbonylalkyl group of 2 to 3 carbon atoms, a lower alkoxycarbonylalkyl group of 3 to 6 carbon atoms, a benzyl group, a benzyl group having 1 to 2 substituents (selected from a halogen atom, a lower alkyl group of 1 to 3 carbon atoms, a lower alkoxy group of 1 to 3 carbon atoms, a nitro group, a lower alkoxycarbonyl group of 2 to 4 carbon atoms, a hydroxycarbonyl group and a phenoxy group), an alpha-methylbenzyl group or a phenethyl group], and provides a process for producing such compounds useful as an agricultural chemical, particularly as a herbicide, as well as processes for producing intermediates for said compounds.
The compounds produced according to the process of the present invention are useful as a herbicide particularly for soybean, as mentioned in U.S. Patent Application Nos. 712,233 and 845,867 and W086/02642.
2. Related Art
Processes for producing triazoline derivatives are disclosed in U.S. Pat. Nos. 4,318,731 and 4,398,943, W086/02642, etc. However, these processes are not preferable for industrial application because they employ many steps and use, as one starting material, an expensive substituted phenylhydrazine wherein the 2-position of the phenyl ring has a fluorine atom substituent.